ES2209124T3 - "3-cianoquinolinas sustituidas". - Google Patents
"3-cianoquinolinas sustituidas".Info
- Publication number
- ES2209124T3 ES2209124T3 ES98914417T ES98914417T ES2209124T3 ES 2209124 T3 ES2209124 T3 ES 2209124T3 ES 98914417 T ES98914417 T ES 98914417T ES 98914417 T ES98914417 T ES 98914417T ES 2209124 T3 ES2209124 T3 ES 2209124T3
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- amino
- cyano
- quinolinecarbonitrile
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 564
- -1 alkenylsulfonamido Chemical group 0.000 claims abstract description 250
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
- 239000001257 hydrogen Substances 0.000 claims abstract description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 37
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 31
- 125000004970 halomethyl group Chemical group 0.000 claims abstract description 30
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 29
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 24
- 125000005042 acyloxymethyl group Chemical group 0.000 claims abstract description 22
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims abstract description 22
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 21
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 14
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 13
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 125000000033 alkoxyamino group Chemical group 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 170
- 239000002253 acid Substances 0.000 claims description 97
- 239000002904 solvent Substances 0.000 claims description 91
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 89
- 229910052799 carbon Inorganic materials 0.000 claims description 79
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 77
- 206010028980 Neoplasm Diseases 0.000 claims description 63
- 125000004429 atom Chemical group 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 150000002431 hydrogen Chemical group 0.000 claims description 58
- 230000005764 inhibitory process Effects 0.000 claims description 41
- 238000011282 treatment Methods 0.000 claims description 36
- 239000012442 inert solvent Substances 0.000 claims description 33
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- ZRTXZWXHWPAXFT-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZRTXZWXHWPAXFT-UHFFFAOYSA-N 0.000 claims description 28
- 238000010438 heat treatment Methods 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 150000008064 anhydrides Chemical class 0.000 claims description 21
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 102000043136 MAP kinase family Human genes 0.000 claims description 15
- 108091054455 MAP kinase family Proteins 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 11
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 230000008029 eradication Effects 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- WMSREFWREGHLAP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WMSREFWREGHLAP-UHFFFAOYSA-N 0.000 claims description 8
- 102000001253 Protein Kinase Human genes 0.000 claims description 8
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 108060006633 protein kinase Proteins 0.000 claims description 8
- UMAUXDSUHUAKMF-UHFFFAOYSA-N chembl111586 Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 UMAUXDSUHUAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- IMBMTYREOJZAAW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 IMBMTYREOJZAAW-UHFFFAOYSA-N 0.000 claims description 6
- 230000017066 negative regulation of growth Effects 0.000 claims description 6
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- AJSYUAVIQGKJFW-UHFFFAOYSA-N 6-amino-4-(3,4-dibromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 AJSYUAVIQGKJFW-UHFFFAOYSA-N 0.000 claims description 5
- PFVDWAYDYKHDEH-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-8-[(dimethylamino)methyl]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(N)=CC2=C1NC1=CC=CC(Br)=C1 PFVDWAYDYKHDEH-UHFFFAOYSA-N 0.000 claims description 5
- OXXUZYBVAKGKQB-UHFFFAOYSA-N 6-amino-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 OXXUZYBVAKGKQB-UHFFFAOYSA-N 0.000 claims description 5
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- IYVDPTGYWDFGTF-VOTSOKGWSA-N (e)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)/C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-VOTSOKGWSA-N 0.000 claims description 4
- IYVDPTGYWDFGTF-SREVYHEPSA-N (z)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)\C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-SREVYHEPSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- RUGCZQOSGFAGFE-UHFFFAOYSA-N 4-(3,4-dibromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 RUGCZQOSGFAGFE-UHFFFAOYSA-N 0.000 claims description 4
- ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCCl)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 0.000 claims description 4
- GEUFKSXFZJFSDI-UHFFFAOYSA-N 4-[3-(hydroxymethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1 GEUFKSXFZJFSDI-UHFFFAOYSA-N 0.000 claims description 4
- JSRLAMXXELZKLJ-UHFFFAOYSA-N 6-amino-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 JSRLAMXXELZKLJ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000004071 biological effect Effects 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- 230000002074 deregulated effect Effects 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- RRPOWKSQIHLYPG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-methylprop-2-enamide Chemical compound C12=CC(NC(=O)C(=C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 RRPOWKSQIHLYPG-UHFFFAOYSA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- WYUJPMJLGOVLKG-UHFFFAOYSA-N 4-(3,4-difluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 WYUJPMJLGOVLKG-UHFFFAOYSA-N 0.000 claims description 3
- PPNMPEHEXLGGID-UHFFFAOYSA-N 4-(3,4-dimethoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PPNMPEHEXLGGID-UHFFFAOYSA-N 0.000 claims description 3
- ZXILYRWRAKLTOG-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 ZXILYRWRAKLTOG-UHFFFAOYSA-N 0.000 claims description 3
- CQKFTSMPIIYOBX-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 CQKFTSMPIIYOBX-UHFFFAOYSA-N 0.000 claims description 3
- IKOYWGLBVGPRAG-UHFFFAOYSA-N 4-(3-bromoanilino)-6-ethoxy-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=CC(Br)=C1 IKOYWGLBVGPRAG-UHFFFAOYSA-N 0.000 claims description 3
- SNLXBZYKYWEIOV-UHFFFAOYSA-N 4-(3-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 SNLXBZYKYWEIOV-UHFFFAOYSA-N 0.000 claims description 3
- BISJVYCVPJVRKJ-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 BISJVYCVPJVRKJ-UHFFFAOYSA-N 0.000 claims description 3
- NUBVTRDETNNCGY-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=CC(Br)=C1 NUBVTRDETNNCGY-UHFFFAOYSA-N 0.000 claims description 3
- OESIRSGDGHCWFH-UHFFFAOYSA-N 4-(3-bromoanilino)-8-[(dimethylamino)methyl]-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 OESIRSGDGHCWFH-UHFFFAOYSA-N 0.000 claims description 3
- AFOMMVJBDXYOAA-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methyl-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 AFOMMVJBDXYOAA-UHFFFAOYSA-N 0.000 claims description 3
- HLBGGOYPNRIHFH-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 HLBGGOYPNRIHFH-UHFFFAOYSA-N 0.000 claims description 3
- FNRKKHMPSZQHEJ-UHFFFAOYSA-N 4-(3-chloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 FNRKKHMPSZQHEJ-UHFFFAOYSA-N 0.000 claims description 3
- CCECSDRSBLPTHW-UHFFFAOYSA-N 4-(3-cyanoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C#N)=C1 CCECSDRSBLPTHW-UHFFFAOYSA-N 0.000 claims description 3
- DLQVSGGYBADFFQ-UHFFFAOYSA-N 4-(3-iodoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 DLQVSGGYBADFFQ-UHFFFAOYSA-N 0.000 claims description 3
- CFEACTBBVRNDBB-UHFFFAOYSA-N 4-(3-methoxyanilino)-6-nitroquinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 CFEACTBBVRNDBB-UHFFFAOYSA-N 0.000 claims description 3
- FMAZODAHMSMUNK-UHFFFAOYSA-N 4-(3-methylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FMAZODAHMSMUNK-UHFFFAOYSA-N 0.000 claims description 3
- PICBGXSASXFIAL-UHFFFAOYSA-N 4-(4-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 PICBGXSASXFIAL-UHFFFAOYSA-N 0.000 claims description 3
- YXCSSHCCXLUHDG-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1C YXCSSHCCXLUHDG-UHFFFAOYSA-N 0.000 claims description 3
- WEOXCMIQDJTOOP-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-nitroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC([N+]([O-])=O)=C1 WEOXCMIQDJTOOP-UHFFFAOYSA-N 0.000 claims description 3
- NPVUUFCFLLPVCM-UHFFFAOYSA-N 6,7-dimethoxy-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(F)(F)F)=C1 NPVUUFCFLLPVCM-UHFFFAOYSA-N 0.000 claims description 3
- LEACUGBTKYYIDG-UHFFFAOYSA-N 6-amino-4-(3,4-difluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 LEACUGBTKYYIDG-UHFFFAOYSA-N 0.000 claims description 3
- IUHXMKMPNZOIIR-UHFFFAOYSA-N 6-amino-4-(3-chloroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 IUHXMKMPNZOIIR-UHFFFAOYSA-N 0.000 claims description 3
- UPINFBFRHUFCMT-UHFFFAOYSA-N 6-amino-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(F)=C1 UPINFBFRHUFCMT-UHFFFAOYSA-N 0.000 claims description 3
- JSCNIEOKVSQSKM-UHFFFAOYSA-N 6-amino-4-(3-iodoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 JSCNIEOKVSQSKM-UHFFFAOYSA-N 0.000 claims description 3
- PNHLUCIDSVSCDW-UHFFFAOYSA-N 6-amino-4-(3-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 PNHLUCIDSVSCDW-UHFFFAOYSA-N 0.000 claims description 3
- YOOVBYGMAALDAY-UHFFFAOYSA-N 6-ethoxy-4-(3-hydroxy-4-methylanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=C(C)C(O)=C1 YOOVBYGMAALDAY-UHFFFAOYSA-N 0.000 claims description 3
- WUVXAOGFNCAWFT-UHFFFAOYSA-N 6-nitro-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 WUVXAOGFNCAWFT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82660497A | 1997-04-03 | 1997-04-03 | |
| US826604 | 1997-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2209124T3 true ES2209124T3 (es) | 2004-06-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98914417T Expired - Lifetime ES2209124T3 (es) | 1997-04-03 | 1998-04-02 | "3-cianoquinolinas sustituidas". |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0973746B1 (pl) |
| JP (2) | JP4537500B2 (pl) |
| KR (1) | KR100531969B1 (pl) |
| CN (1) | CN1121391C (pl) |
| AR (1) | AR012313A1 (pl) |
| AT (1) | ATE250583T1 (pl) |
| AU (1) | AU750906B2 (pl) |
| BR (1) | BR9808478A (pl) |
| CA (1) | CA2285241C (pl) |
| CZ (1) | CZ299136B6 (pl) |
| DE (1) | DE69818442T2 (pl) |
| DK (1) | DK0973746T3 (pl) |
| ES (1) | ES2209124T3 (pl) |
| HU (1) | HU229549B1 (pl) |
| IL (1) | IL132192A0 (pl) |
| NO (1) | NO313827B1 (pl) |
| NZ (1) | NZ337782A (pl) |
| PL (1) | PL196471B1 (pl) |
| PT (1) | PT973746E (pl) |
| RU (1) | RU2202551C2 (pl) |
| SK (1) | SK284922B6 (pl) |
| TR (1) | TR199902946T2 (pl) |
| TW (1) | TWI228492B (pl) |
| UA (1) | UA73073C2 (pl) |
| WO (1) | WO1998043960A1 (pl) |
| ZA (1) | ZA982771B (pl) |
Families Citing this family (379)
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| CA2263479A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Quinoline derivatives inhibiting the effect of growth factors such as vegf |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| US6294532B1 (en) | 1997-08-22 | 2001-09-25 | Zeneca Limited | Oxindolylquinazoline derivatives as angiogenesis inhibitors |
| HRP20010119B1 (hr) | 1998-08-18 | 2008-05-31 | The Regents Of The University Of California | Sprječavanje stvaranja sluzi u dišnim putevima primjenom antagonista egf-r |
| US6288082B1 (en) | 1998-09-29 | 2001-09-11 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| NZ510551A (en) * | 1998-09-29 | 2003-03-28 | American Cyanamid Co | Substituted 3-cyanoquinolines useful as protein tyrosine kinases inhibitors |
| DK2253620T3 (da) | 1998-09-29 | 2014-03-31 | Wyeth Holdings Llc | Substituerede 3-cyanoquinoliner som protein-tyrosinkinase-inhibitorer |
| US6297258B1 (en) | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| AU2004200300A1 (en) * | 1998-09-29 | 2004-02-19 | Wyeth Holdings Corporation | Substituted 3-cyanoquinolines as Protein Tyrosine Kinases Inhibitors |
| GB9904103D0 (en) | 1999-02-24 | 1999-04-14 | Zeneca Ltd | Quinoline derivatives |
| CZ20013079A3 (cs) * | 1999-02-27 | 2001-11-14 | Boehringer Ingelheim Pharma Kg | Deriváty 4-aminochinazolinu a chinolinu |
| RU2001131356A (ru) * | 1999-04-21 | 2003-06-27 | Американ Цианамид Компани (US) | Замещенные 3-циано-[1.7], [1.5] и [1.8] нафтиридиновые ингибиторы тирозинкиназ |
| US6355636B1 (en) | 1999-04-21 | 2002-03-12 | American Cyanamid Company | Substituted 3-cyano-[1.7],[1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases |
| US6548496B2 (en) | 1999-04-21 | 2003-04-15 | American Cyanamid Company | Substituted 3-cyano-[1.7], [1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases |
| GB9910580D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| GB9910577D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| GB9910579D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| SK287010B6 (sk) * | 1999-06-21 | 2009-09-07 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyklické heterocyklické zlúčeniny, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
| US7192698B1 (en) | 1999-08-17 | 2007-03-20 | Purdue Research Foundation | EphA2 as a diagnostic target for metastatic cancer |
| US6927203B1 (en) | 1999-08-17 | 2005-08-09 | Purdue Research Foundation | Treatment of metastatic disease |
| JP3522727B2 (ja) | 1999-11-05 | 2004-04-26 | アストラゼネカ アクチボラグ | Vegf阻害剤としてのキナゾリン誘導体 |
| US6638929B2 (en) | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| CN100432055C (zh) * | 1999-12-29 | 2008-11-12 | 惠氏公司 | 三环蛋白激酶抑制剂 |
| US6384051B1 (en) | 2000-03-13 | 2002-05-07 | American Cyanamid Company | Method of treating or inhibiting colonic polyps |
| BR0109165A (pt) * | 2000-03-13 | 2003-04-22 | American Cyanamid Co | Método de tratamento de pólipos colÈnicos |
| AR035851A1 (es) * | 2000-03-28 | 2004-07-21 | Wyeth Corp | 3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas |
| US6608048B2 (en) | 2000-03-28 | 2003-08-19 | Wyeth Holdings | Tricyclic protein kinase inhibitors |
| US6521618B2 (en) | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| DE60121931T2 (de) | 2000-04-07 | 2007-03-01 | Astrazeneca Ab | Chinazolinverbindungen |
| US6627634B2 (en) | 2000-04-08 | 2003-09-30 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them |
| MXPA02009855A (es) * | 2000-04-08 | 2003-03-27 | Boehringer Ingelheim Pharma | Heterociclos biciclicos, medicamentos que contienen estos compuestos, su empleo y procedimientos para su preparacion. |
| AU2002216758A1 (en) * | 2000-07-03 | 2002-01-14 | Astrazeneca Ab | Quinazolines with therapeutic use |
| US6576644B2 (en) * | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| US7101976B1 (en) | 2000-09-12 | 2006-09-05 | Purdue Research Foundation | EphA2 monoclonal antibodies and methods of making and using same |
| JP2004517059A (ja) | 2000-11-02 | 2004-06-10 | アストラゼネカ アクチボラグ | 抗腫瘍剤用の4−置換キノリン類 |
| WO2002044166A1 (en) | 2000-11-02 | 2002-06-06 | Astrazeneca Ab | Substituted quinolines as antitumor agents |
| US7019012B2 (en) | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| CN100457719C (zh) * | 2000-12-29 | 2009-02-04 | 惠氏公司 | 区域选择性制备取代的苯并[g]喹啉-3-腈和苯并[g]喹唑啉的方法 |
| SE0101675D0 (sv) * | 2001-05-11 | 2001-05-11 | Astrazeneca Ab | Novel composition |
| WO2003000266A1 (en) * | 2001-06-21 | 2003-01-03 | Ariad Pharmaceuticals, Inc. | Novel quinolines and uses thereof |
| EP1412367A4 (en) | 2001-06-21 | 2006-05-03 | Ariad Pharma Inc | NEW CHINOLINE AND ITS USE |
| EP1409481B1 (en) | 2001-07-16 | 2006-10-04 | Astrazeneca AB | Quinoline derivatives and their use as tyrosine kinase inhibitors |
| UA77200C2 (en) | 2001-08-07 | 2006-11-15 | Wyeth Corp | Antineoplastic combination of cci-779 and bkb-569 |
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| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
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1998
- 1998-02-04 UA UA99116029A patent/UA73073C2/uk unknown
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- 1998-04-02 WO PCT/US1998/006480 patent/WO1998043960A1/en not_active Ceased
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- 1998-04-02 JP JP54198198A patent/JP4537500B2/ja not_active Expired - Lifetime
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- 1998-04-02 RU RU99123060/04A patent/RU2202551C2/ru active
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- 1998-04-02 AU AU68777/98A patent/AU750906B2/en not_active Expired
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